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WO2013161703A1 - Procédé de production d'un catalyseur moulé et procédé de production d'un diène ou d'un aldéhyde insaturé et/ou d'un acide carboxylique insaturé l'utilisant - Google Patents

Procédé de production d'un catalyseur moulé et procédé de production d'un diène ou d'un aldéhyde insaturé et/ou d'un acide carboxylique insaturé l'utilisant Download PDF

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Publication number
WO2013161703A1
WO2013161703A1 PCT/JP2013/061624 JP2013061624W WO2013161703A1 WO 2013161703 A1 WO2013161703 A1 WO 2013161703A1 JP 2013061624 W JP2013061624 W JP 2013061624W WO 2013161703 A1 WO2013161703 A1 WO 2013161703A1
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WIPO (PCT)
Prior art keywords
catalyst
producing
molded
reaction
molded catalyst
Prior art date
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PCT/JP2013/061624
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English (en)
Japanese (ja)
Inventor
良太 平岡
由美 日野
公人 奥村
元彦 杉山
大樹 元村
Original Assignee
日本化薬株式会社
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Filing date
Publication date
Application filed by 日本化薬株式会社 filed Critical 日本化薬株式会社
Priority to EP13782624.4A priority Critical patent/EP2842626A4/fr
Priority to JP2014512523A priority patent/JP5970542B2/ja
Priority to US14/396,478 priority patent/US9573127B2/en
Priority to SG11201406832UA priority patent/SG11201406832UA/en
Priority to KR1020147029775A priority patent/KR101745555B1/ko
Priority to CN201380021431.XA priority patent/CN104245127B/zh
Publication of WO2013161703A1 publication Critical patent/WO2013161703A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0215—Coating
    • B01J37/0221—Coating of particles
    • B01J37/0223—Coating of particles by rotation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
    • B01J23/88—Molybdenum
    • B01J23/883—Molybdenum and nickel
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/28—Molybdenum
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/31—Chromium, molybdenum or tungsten combined with bismuth
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
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    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/85—Chromium, molybdenum or tungsten
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    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0027—Powdering
    • B01J37/0045—Drying a slurry, e.g. spray drying
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/03—Precipitation; Co-precipitation
    • B01J37/038—Precipitation; Co-precipitation to form slurries or suspensions, e.g. a washcoat
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/12—Alkadienes
    • C07C11/16—Alkadienes with four carbon atoms
    • C07C11/167—1, 3-Butadiene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C47/22—Acryaldehyde; Methacryaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
    • C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
    • C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the alkali- or alkaline earth metals or beryllium
    • C07C2523/04—Alkali metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
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    • C07C2523/74—Iron group metals
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    • C—CHEMISTRY; METALLURGY
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    • C07C2523/75—Cobalt
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    • C07C2523/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
    • C07C2523/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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Definitions

  • the present invention relates to a method for producing a molded catalyst used for the production of dienes or unsaturated aldehydes and / or unsaturated carboxylic acids.
  • Unsaturated carboxylic acids such as acrylic acid and methacrylic acid used as raw materials for various chemicals can be produced by a two-step reaction using an unsaturated aldehyde as an intermediate product.
  • Acrylic acid and methacrylic acid are both steadily increasing in demand, and therefore the catalyst used for production is being improved energetically.
  • butadiene an important chemical raw material used as a raw material for synthetic rubber and the like, has been rapidly increasing in demand as a raw material for energy-saving automobile tires in recent years due to increasing global automobile demand and environmental awareness. Yes.
  • the production amount of the C4 fraction is decreasing, the shortage of butadiene production continues, and it is expected that the shortage of butadiene supply will accelerate further in the future. For this reason, industrialization of a new butadiene production method is strongly desired.
  • a method for producing an unsaturated aldehyde and / or an unsaturated carboxylic acid by a selective oxidation reaction of an unsaturated hydrocarbon in a fixed bed reactor using a composite metal oxide catalyst containing molybdenum as an essential component is well known. Further, a method for producing butadiene from n-butene in a fixed bed reactor using a composite metal oxide catalyst containing molybdenum as an essential component is also well known.
  • the shape of the catalyst used in the fixed bed reactor is selected according to the application, but there are ring shape, cylinder shape, tablet shape, honeycomb shape, three-leaf type, four-leaf type, and even a spherical catalyst shape. Well used.
  • spherical catalysts are widely used because of the ease of filling the reaction tube with the catalyst and removing the used catalyst from the reaction tube.
  • the method of supporting and molding a catalytically active component on an inert carrier is widely used industrially for the purpose of reducing the heat storage of the catalyst layer, etc. in use. In particular, it is used as an effective method when an objective product is selectively produced by an oxidation reaction or oxidative dehydrogenation reaction of an organic compound.
  • Patent Document 1 discloses a method for producing acrolein and / or acrylic acid from propylene
  • Patent Document 2 discloses methacrolein and / or methacryl from isobutylene and / or tertiary butyl alcohol.
  • a method for producing a catalyst for producing an acid is disclosed.
  • Patent Documents 1 and 2 a production method by a rolling granulation method is disclosed as a method for producing a spherical shaped catalyst.
  • a spherical carrier necessary for obtaining a desired catalyst particle size is put into a rolling granulator, and a liquid serving as a binder and a catalytically active component and / or precursor thereof are used as a carrier while rotating a molding machine.
  • a spherical shaped catalyst is produced by sprinkling.
  • Patent Document 3 and Patent Document 4 describe a method of oxidative dehydrogenation in the presence of a composite metal oxide catalyst mainly composed of molybdenum, bismuth, iron and cobalt.
  • a composite metal oxide catalyst mainly composed of molybdenum, bismuth, iron and cobalt.
  • Patent Document 5 describes a coated molded catalyst produced by mixing a pore-forming agent, and describes production on an industrial scale.
  • Patent Document 5 does not clearly show the effect on the conversion rate of butene and the selectivity of butadiene by the production of the coating molded catalyst by mixing the pore forming agent. Further, in the method for producing a coated molded catalyst cited in Patent Document 5, the relative centrifugal acceleration is extremely low as compared with the method of this patent, which is a problem in terms of practical mechanical strength. It is an object of the present invention to provide a method for producing a shaped catalyst having sufficient mechanical strength and catalyst performance.
  • the present inventors have demonstrated that a catalyst produced by giving a specific relative centrifugal acceleration by adjusting the diameter (rotation radius) and rotation speed of a rolling granulator in the production process of a molded catalyst has high catalyst performance.
  • the present invention has been completed. That is, the present invention (1) Fixed bed oxidation reaction or fixed bed oxidation dehydration in which a catalyst powder containing a composite metal oxide containing molybdenum as an essential component is supported on an inert carrier by a rolling granulation method at a relative centrifugal acceleration of 1 to 35G.
  • the method of manufacturing molded catalyst according to the composite metal oxide has a composition represented by the following formula (1) (1) Mo a Bi b Ni c Co d Fe f X g Y h O x formula (1)
  • Mo, Bi, Ni, Co, Fe and O represent molybdenum, bismuth, nickel, cobalt, iron and oxygen, respectively
  • X is tungsten, antimony, tin, zinc, chromium, manganese, magnesium
  • Y represents at least one element selected from the group consisting of potassium, rubidium, calcium, barium, thallium and cesium
  • b, c, d, f, g, h and x represent the number of atoms of molybdenum, bismuth, nickel, cobalt, iron, X, Y
  • the produced molded catalyst is converted into n-butene by oxidative dehydrogenation.
  • Unsaturated aldehyde and / or unsaturated which is oxidized to the corresponding unsaturated aldehyde and / or unsaturated carboxylic acid by gas phase catalytic oxidation reaction using the molded catalyst obtained by the production method described in (6)
  • the present invention relates to a method for producing carboxylic acid.
  • a molded catalyst having sufficient mechanical strength and catalyst performance can be produced.
  • the composite metal oxide contained in the catalyst powder in the molded catalyst obtained in the present invention contains molybdenum as an essential element, other constituent elements and the constituent ratio thereof are not particularly limited, but preferably the following general formula (1 ) Mo a Bi b Ni c Co d Fe f X g Y h O x formula (1) (Wherein Mo, Bi, Ni, Co, Fe and O represent molybdenum, bismuth, nickel, cobalt, iron and oxygen, respectively, X is tungsten, antimony, tin, zinc, chromium, manganese, magnesium, silicon, aluminum Represents at least one element selected from the group consisting of cerium, tellurium, boron, germanium, zirconium and titanium, and Y represents at least one element selected from the group consisting of potassium, rubidium, calcium, barium, thallium and cesium , A, b, c, d, f, g, h and x represent the number of atoms of molybden
  • the powder containing the catalytically active component is prepared by a known method such as a coprecipitation method or a spray drying method.
  • nitrates, ammonium salts, hydroxides, oxides, acetates, and the like of various metal elements such as molybdenum, bismuth, nickel, cobalt, iron, X, and Y can be used, and are not particularly limited.
  • Liquids or slurries containing different types of catalytically active components can be prepared by changing the type and / or amount of metal salt supplied to water, and powder containing the catalytically active components can be obtained by spray drying or the like.
  • the powder thus obtained can be calcined at 200 to 600 ° C., preferably 300 to 500 ° C., preferably in air or a nitrogen stream, to obtain a catalytically active component (hereinafter referred to as pre-calcined powder).
  • the pre-fired powder thus obtained can be used as a catalyst as it is, but in the present invention, it is molded in consideration of production efficiency and workability.
  • the shape of the molded product is not particularly limited as long as the catalyst component can be coated, but it is preferably spherical from the viewpoint of production and actual use.
  • pre-baked powders of differently prepared granules with different component compositions may be mixed and molded in any proportion.
  • a method may be employed in which the operation of supporting different kinds of pre-fired powder on an inert carrier is repeated to form the pre-fired powder into a multilayer.
  • a molding aid such as crystalline cellulose and / or a strength improver such as a ceramic whisker.
  • the amount of the molding aid and / or strength improver used is preferably 30% by weight or less with respect to the pre-fired powder.
  • the molding aid and / or the strength improver may be mixed in advance with the above pre-fired powder before molding, or may be added at the same time as or before or after the pre-fired powder is added to the molding machine. That is, if the molded catalyst finally used in the reaction is within the range of desired catalyst physical properties and / or catalyst composition, the above-mentioned molded product shape and molding method can be employed.
  • a method in which the catalyst powder is coated and molded on the support by adding a pre-baked powder and, if necessary, a molding aid and a strength improver is preferable.
  • binders that can be used include water, ethanol, methanol, propanol, polyhydric alcohol, polymer binder polyvinyl alcohol, silica sol aqueous solution of inorganic binder, etc.
  • ethanol, methanol, propanol, polyhydric alcohol Alcohols are preferred, diols such as ethylene glycol and triols such as glycerin are more preferred, and aqueous solutions having a glycerin concentration of 5% by weight or more are particularly preferred.
  • the amount of these binders used is usually 2 to 60 parts by weight based on 100 parts by weight of the pre-fired powder, but 10 to 50 parts by weight is preferable in the case of an aqueous glycerin solution.
  • the binder may be added to the tumbling granulator at the same time as the pre-fired powder, or may be added alternately with the pre-fired powder.
  • the size of the inert carrier is usually about 2 to 20 mm, on which the pre-fired powder is supported.
  • the loading ratio is determined in consideration of the catalyst use conditions such as space velocity and feed hydrocarbon concentration. Usually, it is preferably supported so as to be 10 to 80% by weight.
  • the relative centrifugal acceleration applied when rolling granulation is usually 1G to 35G, preferably 1.2G to 30G, more preferably 1.5G to 20G.
  • the relative centrifugal acceleration is a numerical value representing the magnitude of the centrifugal force per unit weight when the carrier is put in a rolling granulator and rotated by the device, as a ratio with the gravitational acceleration. Is represented by the following formula (3). This increases in proportion to the absolute value of the distance from the center of rotation of the device and the square of the rotational speed.
  • RCF 1118 ⁇ r ⁇ N 2 ⁇ 10 ⁇ 8 formula (3)
  • RCF represents a relative centrifugal acceleration (G)
  • r represents a distance (cm) from the center of rotation
  • N represents a rotation speed (rpm).
  • G relative centrifugal acceleration
  • rpm rotation speed
  • the relative centrifugal acceleration can be adjusted by increasing the rotational speed.
  • the radius of rotation is not particularly limited, in practice, it is easy to use a commercially available device, and it is usually preferably about 0.1 to 2 m.
  • the rotational speed is determined so as to be in the relative centrifugal acceleration range according to the formula (3) according to the size of the molding machine to be used.
  • the input amount of the inert carrier to the molding machine is appropriately set according to the size of the molding machine, a desired production rate, etc., but it is preferably carried out in the range of 0.1 to 100 kg.
  • Patent Document 5 also suggests that a coated molded catalyst containing molybdenum is produced by a rolling granulation method. However, the rotational speed at the time of rolling granulation is extremely slow compared with the method of the present invention. Therefore, the relative centrifugal acceleration is extremely low as compared with the method of the present invention.
  • the molded catalyst that has undergone the tumbling granulation process can be charged into the reactor as it is, but in order to avoid high temperatures due to the burning of binders remaining in the catalyst during heating, and to ensure operational safety and health From the standpoint of securing practical strength, it is preferable to calcine again before using the molded catalyst that has undergone the rolling granulation step for the reaction.
  • the firing temperature at the time of firing again is 450 to 650 ° C., the firing time is 3 to 30 hours, preferably 4 to 15 hours, and is appropriately set according to the reaction conditions to be used.
  • the firing atmosphere may be either an air atmosphere or a nitrogen atmosphere, but industrially an air atmosphere is preferred.
  • the catalyst of the present invention thus obtained has high mechanical strength.
  • the friability is preferably 3% by weight or less, more preferably 1.5% by weight or less, and still more preferably 0.5% by weight or less.
  • the catalyst of the present invention thus obtained is a step of producing acrolein and acrylic acid by vapor-phase catalytic oxidation of propylene with molecular oxygen or a molecular oxygen-containing gas, or a solid acid catalyst such as isobutylene or the catalyst of the present invention.
  • a step of producing methacrolein and methacrylic acid by vapor-phase catalytic oxidation of tertiary butyl alcohol, which is known to easily convert to isobutylene and water, with molecular oxygen or a molecular oxygen-containing gas, or n-butene Can be used in a process for producing butadiene by gas phase catalytic oxidative dehydrogenation reaction with molecular oxygen or a molecular oxygen-containing gas.
  • the flow method of the raw material gas may be a normal single-flow method or a recycling method, and can be carried out under generally used conditions and is not particularly limited.
  • propylene as a starting material is 1 to 10% by volume at room temperature, preferably 4 to 9% by volume, molecular oxygen is 3 to 20% by volume, preferably 4 to 18% by volume, water vapor is 0 to 60% by volume, Preferably, 4 to 50% by volume, and a gas mixture of 20 to 80% by volume, preferably 30 to 60% by volume of an inert gas such as carbon dioxide and nitrogen, is charged on the catalyst of the present invention to 250 to 250%.
  • the reaction can be carried out at 450 ° C. under normal pressure to 10 atm and a space velocity of 300 to 5000 h ⁇ 1 .
  • n-butene as a starting material is 1 to 16% by volume, preferably 3 to 12% by volume, and molecular oxygen is 1 to 20% by volume, preferably 5% at room temperature.
  • the reaction can be carried out by introducing the catalyst of the present invention filled in a tube at a space velocity of 300 to 5000 h ⁇ 1 at 250 to 450 ° C. and a pressure of normal pressure to 10 atm.
  • the target compound in the case of an oxidation reaction in which the raw material compound is propylene, the target compound is (acrolein + acrylic acid).
  • the target compound in the oxidation reaction in which the raw material compound is isobutylene and / or tertiary butyl alcohol is (methacrolein + methacrylic acid).
  • the target compound in the case of an oxidative dehydrogenation reaction using n-butene as the starting compound, the target compound is butadiene.
  • Example 1 Manufacture of catalyst While heating and stirring 3000 parts by weight of distilled water, 423.8 parts by weight of ammonium molybdate tetrahydrate and 3.0 parts by weight of potassium nitrate were dissolved to obtain an aqueous solution (A1). Separately, 302.7 parts by weight of cobalt nitrate hexahydrate, 162.9 parts by weight of nickel nitrate hexahydrate, and 145.4 parts by weight of ferric nitrate nonahydrate were dissolved in 1000 parts by weight of distilled water to prepare an aqueous solution.
  • Aqueous solution (C1) was prepared by dissolving 164.9 parts by weight of bismuth nitrate pentahydrate in 200 parts by weight of distilled water acidified by adding (B1) and 42 parts by weight of concentrated nitric acid. (B1) and (C1) are mixed with the above aqueous solution (A1) successively with vigorous stirring, and the resulting suspension is dried using a spray drier and calcined at 440 ° C. for 6 hours to obtain a pre-calcined powder (D1) Got.
  • the powder obtained by mixing 100 parts by weight of the pre-fired powder with 5 parts by weight of crystalline cellulose is defined by the above formula (2) as an inert carrier (spherical substance having a diameter of 4.5 mm mainly composed of alumina and silica).
  • the weight of the carrier used for molding and the weight of the pre-fired powder were adjusted so that the loading ratio accounted for 50% by weight.
  • a 20 wt% aqueous glycerin solution was used as a binder and supported and molded into a spherical shape with a diameter of 5.2 mm to obtain a molded catalyst (E1).
  • a cylindrical molding machine having a diameter of 23 cm was used for support molding, and the number of rotations of the bottom plate was 150 rpm. The relative centrifugal acceleration at this time was 2.9G.
  • the molded catalyst (F1) was obtained by calcining the molded catalyst (E1) at an calcination temperature of 510 ° C. for 4 hours in an air atmosphere.
  • Example 2 A molded catalyst (F2) was produced in the same manner as in Example 1 except that the number of rotations of the bottom plate during molding was 210 rpm and the relative centrifugal acceleration was 5.7 G. Table 1 shows the oxidation reaction test results and strength measurement results of the molded catalyst F2.
  • Example 3 A molded catalyst (F3) was produced in the same manner as in Example 1 except that the number of rotations of the bottom plate during molding was 260 rpm and the relative centrifugal acceleration was 8.7 G. Table 1 shows the oxidation reaction test results and strength measurement results of the molded catalyst (F3).
  • Example 4 A molded catalyst (F4) was produced in the same manner as in Example 1 except that the number of rotations of the bottom plate during molding was 430 rpm and the relative centrifugal acceleration was 24 G. Table 1 shows the oxidation reaction test results and strength measurement results of the molded catalyst (F4).
  • Comparative Example 1 A molded catalyst (V1) was produced in the same manner as in Example 1 except that the number of revolutions of the bottom plate during molding was 75 rpm and the relative centrifugal acceleration was 0.72 G. Table 1 shows the oxidation reaction test results and strength measurement results of the molded catalyst (V1).
  • Example 5 Manufacture of catalyst While heating and stirring 12,000 parts by weight of distilled water, 3000 parts by weight of ammonium molybdate tetrahydrate and 55.2 parts by weight of cesium nitrate were dissolved to obtain an aqueous solution (A2). Separately, 2782 parts by weight of cobalt nitrate hexahydrate, 1144 parts by weight of ferric nitrate nonahydrate, and 412 parts by weight of nickel nitrate hexahydrate were dissolved in 2300 parts by weight of distilled water to prepare an aqueous solution (B2).
  • An aqueous solution (C2) was prepared by dissolving 1167 parts by weight of bismuth nitrate pentahydrate in 1215 parts by weight of distilled water made acidic by adding 397 parts by weight of concentrated nitric acid.
  • B2) and (C2) were sequentially mixed with the aqueous solution (A2) while vigorously stirring the aqueous solution (A2), the resulting suspension was dried using a spray dryer, and the resulting powder was 460 ° C.
  • the powder obtained by mixing 100 parts by weight of the pre-fired powder with 5 parts by weight of crystalline cellulose is defined by the above formula (2) as an inert carrier (spherical substance having a diameter of 4.5 mm mainly composed of alumina and silica).
  • the weight of the carrier used for molding and the weight of the pre-fired powder were adjusted so that the loading ratio accounted for 50% by weight.
  • a molded catalyst (E5) was obtained by being supported and molded into a spherical shape having a diameter of 5.2 mm.
  • a cylindrical molding machine having a diameter of 23 cm was used for support molding, and the number of rotations of the bottom plate was 260 rpm.
  • the relative centrifugal acceleration at this time was 8.7G.
  • the molded catalyst (E5) was calcined in an air atmosphere at a calcining temperature of 500 ° C. for 4 hours to obtain a molded catalyst (F5).
  • Example 6 A molded catalyst (F6) was produced in the same manner as in Example 5 except that the number of rotations of the bottom plate during molding was 430 rpm and the relative centrifugal acceleration was 23.8 G. Table 1 shows the oxidation reaction test results and strength measurement results of the molded catalyst (F6).
  • Example 7 Manufacture of catalyst
  • a molded catalyst (F7) was produced with a rotational speed of the bottom plate at the time of molding of 260 rpm and a relative centrifugal acceleration of 8.7 G.
  • Table 1 shows the results of the oxidative dehydrogenation reaction test and strength measurement of the molded catalyst (F7) carried out by the method described below.
  • a gas in which the supply amounts of 1-butene, air, water, and nitrogen are set so that the raw material molar ratio is 1-butene: oxygen: nitrogen: water 1: 2.1: 10.4: 2.5
  • the catalyst was introduced into the oxidation reactor at a space velocity of 1440 h ⁇ 1 , the reactor outlet pressure was set to 0 kPaG, and the catalyst performance was evaluated 15 hours after the start of the reaction.
  • Example 8 A molded catalyst (F8) was produced in the same manner as in Example 7, except that the number of rotations of the bottom plate during molding was 430 rpm and the relative centrifugal acceleration was 23.8 G. Table 1 shows the results of the oxidative dehydrogenation reaction test and the strength measurement performed in the same manner as in Example 7 using the molded catalyst (F8).
  • Comparative Example 2 A molded catalyst (V2) was produced in the same manner as in Example 7, except that the number of rotations of the bottom plate during molding was 550 rpm and the relative centrifugal acceleration was 38.9 G. Table 1 shows the results of the oxidative dehydrogenation reaction test and the strength measurement performed in the same manner as in Example 7 using the molded catalyst (V2).
  • Comparative Example 3 A molded catalyst (V3) was produced in the same manner as in Example 7, except that the number of rotations of the bottom plate during molding was 60 rpm and the relative centrifugal acceleration was 0.46 G. Table 1 shows the results of the oxidative dehydrogenation reaction test and the strength measurement performed in the same manner as in Example 7 using the molded catalyst (V3).
  • the shaped catalyst produced by the method of the present invention is a catalyst for producing acrolein and / or acrylic acid from propylene, methacrolein and / or methacrylic acid from isobutylene and / or tertiary butyl alcohol, or butadiene from n-butene. Useful as.

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Abstract

Cette invention concerne un procédé de production d'un catalyseur moulé destiné à servir dans une réaction d'oxydation en lit fixe ou dans une réaction de déshydrogénation oxydative en lit fixe et qui a à la fois une résistance mécanique et une performance catalytique suffisantes. Le catalyseur est produit en faisant supporter une poudre catalytique contenant un oxyde de métal complexe contenant du molybdène à titre de composant obligatoire sur un support inactif par un procédé de granulation par culbute à une accélération centrifuge de 1 à 35 G.
PCT/JP2013/061624 2012-04-23 2013-04-19 Procédé de production d'un catalyseur moulé et procédé de production d'un diène ou d'un aldéhyde insaturé et/ou d'un acide carboxylique insaturé l'utilisant WO2013161703A1 (fr)

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EP13782624.4A EP2842626A4 (fr) 2012-04-23 2013-04-19 Procédé de production d'un catalyseur moulé et procédé de production d'un diène ou d'un aldéhyde insaturé et/ou d'un acide carboxylique insaturé l'utilisant
JP2014512523A JP5970542B2 (ja) 2012-04-23 2013-04-19 成型触媒の製造方法および該成型触媒を用いるジエンまたは不飽和アルデヒドおよび／または不飽和カルボン酸の製造方法
US14/396,478 US9573127B2 (en) 2012-04-23 2013-04-19 Process for producing shaped catalyst and process for producing diene or unsaturated aldehyde and/or unsaturated carboxylic acid using the shaped catalyst
SG11201406832UA SG11201406832UA (en) 2012-04-23 2013-04-19 Method for producing molded catalyst and method for producing diene or unsaturated aldehyde and/or unsaturated carboxylic acid using said molded catalyst
KR1020147029775A KR101745555B1 (ko) 2012-04-23 2013-04-19 성형 촉매의 제조 방법 및 당해 성형 촉매를 이용하는 디엔 또는 불포화 알데히드 및/또는 불포화 카본산의 제조 방법
CN201380021431.XA CN104245127B (zh) 2012-04-23 2013-04-19 成形催化剂的制造方法及使用该成形催化剂的二烯或不饱和醛和/或不饱和羧酸的制造方法

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CN104245127B (zh) 2016-03-30
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CN104245127A (zh) 2014-12-24
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JPWO2013161702A1 (ja) 2015-12-24
TWI574731B (zh) 2017-03-21
SA113340492B1 (ar) 2016-03-03
TW201412396A (zh) 2014-04-01
SG11201406832UA (en) 2014-11-27
US20150126774A1 (en) 2015-05-07
US9573127B2 (en) 2017-02-21
TW201406455A (zh) 2014-02-16
JPWO2013161703A1 (ja) 2015-12-24
JP5970542B2 (ja) 2016-08-17
JP6034372B2 (ja) 2016-11-30
TWI569872B (zh) 2017-02-11
KR20150008864A (ko) 2015-01-23

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